EP2938656B1 - Molecularly imprinted polymers of sol-gel type and their use as antidandruff agent - Google Patents
Molecularly imprinted polymers of sol-gel type and their use as antidandruff agent Download PDFInfo
- Publication number
- EP2938656B1 EP2938656B1 EP13821474.7A EP13821474A EP2938656B1 EP 2938656 B1 EP2938656 B1 EP 2938656B1 EP 13821474 A EP13821474 A EP 13821474A EP 2938656 B1 EP2938656 B1 EP 2938656B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- silane
- acid
- alkyl
- fatty acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 229920000344 molecularly imprinted polymer Polymers 0.000 title claims description 28
- 229920000642 polymer Polymers 0.000 claims description 41
- 239000005642 Oleic acid Substances 0.000 claims description 36
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 36
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 33
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 32
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 32
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 32
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 210000004761 scalp Anatomy 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 19
- 239000000194 fatty acid Substances 0.000 claims description 19
- 229930195729 fatty acid Natural products 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- -1 (C1-C4)alkyl orthosilicates Chemical class 0.000 claims description 18
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910000077 silane Inorganic materials 0.000 claims description 17
- 208000001840 Dandruff Diseases 0.000 claims description 16
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 8
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 241000555676 Malassezia Species 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 6
- BHWUCEATHBXPOV-UHFFFAOYSA-N 2-triethoxysilylethanamine Chemical compound CCO[Si](CCN)(OCC)OCC BHWUCEATHBXPOV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 229910052605 nesosilicate Inorganic materials 0.000 claims description 4
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 claims description 3
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 claims description 3
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- HUPGCAGBHBJUJC-UHFFFAOYSA-N 3-(3-trimethoxysilylpropoxy)aniline Chemical compound CO[Si](OC)(OC)CCCOC1=CC=CC(N)=C1 HUPGCAGBHBJUJC-UHFFFAOYSA-N 0.000 claims description 2
- CNODSORTHKVDEM-UHFFFAOYSA-N 4-trimethoxysilylaniline Chemical compound CO[Si](OC)(OC)C1=CC=C(N)C=C1 CNODSORTHKVDEM-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 28
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 210000000434 stratum corneum Anatomy 0.000 description 15
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 description 13
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 description 13
- 229920002079 Ellagic acid Polymers 0.000 description 12
- 235000004132 ellagic acid Nutrition 0.000 description 12
- 229960002852 ellagic acid Drugs 0.000 description 12
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000000499 gel Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000002245 particle Substances 0.000 description 7
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- OIQJEQLSYJSNDS-UHFFFAOYSA-N piroctone Chemical compound CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O OIQJEQLSYJSNDS-UHFFFAOYSA-N 0.000 description 4
- 101150025733 pub2 gene Proteins 0.000 description 4
- 229910000338 selenium disulfide Inorganic materials 0.000 description 4
- JNMWHTHYDQTDQZ-UHFFFAOYSA-N selenium sulfide Chemical compound S=[Se]=S JNMWHTHYDQTDQZ-UHFFFAOYSA-N 0.000 description 4
- 229960005265 selenium sulfide Drugs 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- 239000012798 spherical particle Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical class [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- BTSZTGGZJQFALU-UHFFFAOYSA-N piroctone olamine Chemical compound NCCO.CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O BTSZTGGZJQFALU-UHFFFAOYSA-N 0.000 description 3
- 229940081510 piroctone olamine Drugs 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical class [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 3
- 229910052711 selenium Chemical class 0.000 description 3
- 239000011669 selenium Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- ZZLOQICNGDMUBA-UHFFFAOYSA-N tetraethyl silicate;hydrate Chemical compound O.CCO[Si](OCC)(OCC)OCC ZZLOQICNGDMUBA-UHFFFAOYSA-N 0.000 description 3
- 229940043810 zinc pyrithione Drugs 0.000 description 3
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- SNUSZUYTMHKCPM-UHFFFAOYSA-N 1-hydroxypyridin-2-one Chemical class ON1C=CC=CC1=O SNUSZUYTMHKCPM-UHFFFAOYSA-N 0.000 description 2
- DMPZOHHHRRENRS-UHFFFAOYSA-N 2,3-Di-O-methylellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(OC)C(OC)=C4OC(=O)C3=C1 DMPZOHHHRRENRS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000555688 Malassezia furfur Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 229950001046 piroctone Drugs 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 238000003980 solgel method Methods 0.000 description 2
- 150000004763 sulfides Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- WLSLSHYMTUVYSP-ZANVPECISA-N 3,3'-di-O-methylellagic acid Natural products COC1=C(O)C=C2[C@@H]3[C@@H]1OC(=O)c4cc(O)c(OC)c(OC2=O)c34 WLSLSHYMTUVYSP-ZANVPECISA-N 0.000 description 1
- LXEQIOGTMDLLEC-UHFFFAOYSA-N 3,4,3'-Tri-O-methylellagic acid Chemical compound OC1=C(OC)C(OC2=O)=C3C4=C2C=C(OC)C(OC)=C4OC(=O)C3=C1 LXEQIOGTMDLLEC-UHFFFAOYSA-N 0.000 description 1
- KLAGYIBJNXLDTL-UHFFFAOYSA-N 3,8-di-o-methylellagic acid Chemical compound O1C(=O)C2=CC(O)=C(OC)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 KLAGYIBJNXLDTL-UHFFFAOYSA-N 0.000 description 1
- XPFCZYUVICHKDS-UHFFFAOYSA-N 3-methylbutane-1,3-diol Chemical compound CC(C)(O)CCO XPFCZYUVICHKDS-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000007353 Magnolia ovalis Species 0.000 description 1
- 241001291474 Malassezia globosa Species 0.000 description 1
- 241001159568 Malassezia sp. Species 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- 206010029216 Nervousness Diseases 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
- 229910018210 SexSy Inorganic materials 0.000 description 1
- 206010040844 Skin exfoliation Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- NDXSDWFOYZXARW-UHFFFAOYSA-N Trimethylellagsaeure Natural products COC1=C(OC)C(OC2=O)=C3C4=C2C=C(OC)C(O)=C4OC(=O)C3=C1 NDXSDWFOYZXARW-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004964 aerogel Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical compound ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
- 230000001496 desquamative effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940108623 eicosenoic acid Drugs 0.000 description 1
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 229920000592 inorganic polymer Polymers 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 244000005706 microflora Species 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000002077 nanosphere Substances 0.000 description 1
- 239000002353 niosome Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 229960002026 pyrithione Drugs 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/32—Post-polymerisation treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
Definitions
- a subject matter of the invention is specific molecularly imprinted polymers of sol-gel type and also a cosmetic composition comprising them, and their use for eliminating or reducing dandruff of the scalp.
- dandruff corresponding to a desquamative disorder of the scalp, is disagreeable both aesthetically and because of the annoyance which it causes (itching, redness, and the like), so that many people confronted with this problem to variable degrees wish to be rid of it efficiently and permanently.
- Dandruff corresponds to an excessive and visible desquamation of the scalp resulting from excessively rapid multiplication of the epidermal cells.
- This phenomenon can be caused in particular by microtraumas of physical or chemical nature, such as excessively aggressive hair treatments, extreme climatic conditions, nervousness, diet, fatigue or pollution, but it has been demonstrated that dandruff conditions usually result from a disorder of the microflora of the scalp and more particularly from the excessive colonization of a yeast which belongs to the family of yeasts of the Malassezia genus (previously known as Pityrosporum ovale) and which is naturally present on the scalp.
- antifungal agents used for their antifungal action, of zinc pyrithione, piroctone olamine or selenium disulfide.
- antidandruff agents used for their antifungal action, of zinc pyrithione, piroctone olamine or selenium disulfide.
- these specific molecularly imprinted polymers make it possible to trap the oleic acid present on the scalp and thus to prevent the colonization of the scalp by Malassezia microorganisms. They thus make it possible to reduce or prevent the appearance of dandruff.
- a subject matter of the present invention is thus a molecularly imprinted polymer capable of being obtained according to a process comprising a first stage of polymerization of a mixture comprising:
- Another subject matter of the invention is a process for the preparation of molecularly imprinted polymer as defined above.
- Another subject matter of the invention is a cosmetic composition
- a cosmetic composition comprising, in a physiologically acceptable medium, a molecularly imprinted polymer as defined above.
- Another subject matter of the invention is a cosmetic method for preventing and/or treating dandruff of the scalp, in particular that caused by yeasts of the Malassezia genus, characterized in that it comprises the application, to the scalp, of an imprinted polymer as defined above or of a cosmetic composition comprising it.
- Another subject matter of the invention is the cosmetic use of imprinted polymer as defined above as active agent for preventing and/or treating dandruff of the scalp.
- Molecularly imprinted polymers or MIPs are materials which are widely used for their applications in the fields of biotechnology, chemistry, chromatography, analytical chemistry and biology ( J. Mol. Recognit., 19, 106-180 (2006 ); Molecularly Imprinted Materials: Science and Technology, Marcel Dekker, NY, M. Yan and O. Ramstrom (2005 )).
- the concept of molecular imprinting relates to Emil Fisher's famous "lock and key fit" principle known since 1894 for enzymes with their ligand ( Advances in Carbohydrate Chemistry and Biochemistry, 1-20 (1994 )).
- Molecular imprinting consists more specifically in producing a polymer which comprises specific cavities in the shape and size of a target molecule or "imprint", also known as template, which serves as gage for the formation of recognition sites exhibiting a complementarity in shape with the imprinted molecule.
- Molecular imprints are polymers prepared from functional monomers polymerized around a molecule, also known as “template”. The monomer is thus chosen so as to develop noncovalent interactions (hydrogen bond, electrostatic, ionic interactions, and nonionic, indeed even of low energy, such as Van der Waals bonds, or ⁇ - ⁇ stacking) with the template.
- the polymerization will subsequently be carried out in a "porogenic" solvent between the monomers complexed with the template and a crosslinking agent, so as to form specific cavities.
- the bonds between the template and the polymerized monomers are subsequently broken by means of suitable solvents to extract the template from the polymer support.
- the extraction of the template molecule then leaves vacant recognition sites with a high affinity for the target molecule.
- the shape and the size of the imprint and also the spatial arrangement of the functional groups inside the recognition cavity are complementary to the template molecule and include sites of specific interactions with this same molecule.
- the polymerization method used to manufacture the molecularly imprinted polymers according to the invention is the sol-gel polymerization process.
- the sol-gel process makes it possible to manufacture an inorganic polymer by simple chemical reactions known to a person skilled in the art (see, for example, Kirk-Othmer Encyclopedia of Chemical Technology, " Sol-Gel Technology", A. C. Pierre, placed online on 07/13/2007, DOI: 10.1002/0471238961.19151208051403.a01.pub2; http://onlinelibrary.wiley.com/doi/10.1002/0471238961.19151208051403.a01.pub2/pdf , and Ullmann's Encyclopedia of Industrial Chemistry, " Aerogels", N. Hüsing and U.
- the molecularly imprinted polymer is prepared from the silane of following formula (I): R 1 Si(OR 2 ) z (R 3 ) x (I) in which:
- R 2 represents an alkyl group comprising from 1 to 4 carbon atoms.
- R 2 represents a linear alkyl group comprising from 1 to 4 carbon atoms.
- R 2 represents the ethyl group.
- R 3 represents an alkyl group comprising from 1 to 4 carbon atoms.
- R 3 represents a linear alkyl group comprising from 1 to 4 carbon atoms.
- R 3 represents the methyl or ethyl group.
- R 1 is an acyclic chain.
- R 1 is a saturated linear C 1 -C 6 hydrocarbon chain substituted by an amine NH 2 group. More preferably, R 1 is a saturated linear C 2 -C 4 hydrocarbon chain substituted by an amine NH 2 group.
- R 1 is a saturated linear C 1 -C 6 hydrocarbon chain substituted by an amine NH 2 group
- R 2 represents an alkyl group comprising from 1 to 4 carbon atoms
- R 3 represents an alkyl group comprising from 1 to 4 carbon atoms.
- z is equal to 3.
- the silane of formula (I) is chosen from 3-aminopropyltriethoxysilane (APTES), 2-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane or N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane.
- APTES 3-aminopropyltriethoxysilane
- AETES 2-aminoethyltriethoxysilane
- 3-aminopropylmethyldiethoxysilane N-(2-aminoethyl)-3-aminopropyltriethoxysilane
- the silane (I) is chosen from 3-aminopropyltriethoxysilane (APTES), 2-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane or N-(2-aminoethyl)-3-aminopropyltriethoxysilane.
- the silane (I) is 3-aminopropyltriethoxysilane (APTES).
- the sol-gel polymerization is carried out in the presence of a crosslinking agent chosen from tetra(C 1 -C 4 )alkyl orthosilicates.
- the crosslinking agent can be chosen from tetraethoxysilane (TEOS) or tetramethoxysilane (TMOS).
- TEOS tetraethoxysilane
- TMOS tetramethoxysilane
- the crosslinking agent is tetraethoxysilane (TEOS).
- the sol-gel polymerization is carried out in the presence of water in order to bring about the hydrolysis of the silane (I) and then its condensation.
- the polymerization can be carried out in the presence of an acid catalyst, in particular in order to accelerate the condensation reaction, such as, for example, inorganic acids, such as hydrochloric acid, or organic acids, such as acetic acid.
- the polymerization can be carried out in the presence of a basic catalyst, such as, for example, aqueous ammonia.
- a basic catalyst such as, for example, aqueous ammonia.
- This polymer is carried out according to chemical reactions known to a person skilled in the art which are triggered when the reactants are brought into contact with water and optionally with a catalyst which has the effect 1) of hydrolyzing the alkoxy (OR 2 ) groups of the silanes to give hydroxyl groups and then 2) of condensing the hydrolyzed products to result 3) in the polymerization of the system.
- the process for the preparation of the molecularly imprinted polymers is advantageously carried out at a temperature of between 20 and 150°C inclusively.
- the C 14 -C 20 fatty acid, the silane (I) and the crosslinking agent tetra(C 1 -C 4 )alkyl orthosilicate are employed according to a C 14 -C 20 fatty acid/silane (I)/tetra(C 1 -C 4 )alkyl orthosilicate molar ratio ranging from 1/[1 to 20]/[1 to 40], preferably ranging from 1/[1 to 10]/[1 to 30] and preferentially ranging from 1/[1 to 5]/[1 to 5].
- the molecularly imprinted sol-gel polymers are prepared from a porogenic solvent which preferably has a polarity which makes it possible i) to dissolve the C 14 -C 20 fatty acid imprint molecule and/or ii) which is suitable for the interaction of said C 14 -C 20 fatty acid imprint molecule with the molecularly imprinted polymer.
- Porogenic solvent is understood to mean a solvent capable of creating a porous network able to convey the C 14 -C 20 fatty acid molecules as far as the imprints of the polymer.
- the porogenic solvent should also promote the C 14 -C 20 fatty acid imprint molecule/monomer interactions and the stability of the complex formed.
- the porogenic solvent when the dissolution of the imprint molecule in the prepolymerization mixture demands it, is chosen from polar protic organic solvents, such as water or C 1 -C 8 alcohols, such as ethanol.
- the porogenic solvent is a polar aprotic solvent, such as acetonitrile, tetrahydrofuran (THF), dialkylformamides (dimethylformamide, diethylformamide), N-methyl-2-pyrrolidinone (NMP), N-ethyl-2-pyrrolidinone (NEP), N,N'-dimethylpropyleneurea (DMPU) and dimethyl sulfoxide (DMSO).
- THF tetrahydrofuran
- NMP N-methyl-2-pyrrolidinone
- NEP N-ethyl-2-pyrrolidinone
- DMPU N,N'-dimethylpropyleneurea
- DMSO dimethyl sulfoxide
- the porogenic solvent used according to the invention is a solvent chosen from polar (a)protic solvents, such as water, C 1 -C 8 alcohols, such as ethanol, and acetonitrile, and their mixtures.
- polar (a)protic solvents such as water, C 1 -C 8 alcohols, such as ethanol, and acetonitrile, and their mixtures.
- the aim of the invention is to make available a molecularly imprinted polymer which captures saturated or unsaturated fatty C 14 -C 20 carboxylic acids, in particular oleic acid, at the surface of the scalp.
- the fatty C 14 -C 20 carboxylic acids "template” is a compound which mimics oleic acid, which causes dandruff, within the molecularly imprinted polymer in order for the molecularly imprinted polymer subsequently to be able to capture oleic acid when it is applied to the scalp.
- fatty C 14 -C 20 carboxylic acid of myristic acid (C14:0), myristoleic acid (C14:1), pentadecanoic acid (C15:0), palmitic acid (C16:0), palmitoleic acid (C16:1), sapienic acid (C16:1), heptadecanoic acid (or margaric acid) (C17:0), stearic acid (C18:0), oleic acid (C18:1), arachidic acid (C20:0) or eicosenoic acid (C20:1).
- the fatty acid is oleic acid.
- the process for the preparation of the imprinted polymer according to the invention comprises:
- the withdrawal stage is carried out by washing the polymer obtained in the first stage with a washing solvent.
- the washing solvent can be chosen from C 1 -C 4 alcohols, water, acetonitrile, tetrahydrofuran (THF), dialkylformamides (dimethylformamide, diethylformamide), N-methyl-2-pyrrolidinone (NMP), N-ethyl-2-pyrrolidinone (NEP), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), chloroform, acetic acid, aqueous ammonia, diethylamine, and their mixtures.
- the imprinted polymer no longer comprises the C 14 -C 20 fatty acid.
- the empty imprints thus make it possible for the polymer to be able to capture oleic acid when it is applied to the scalp.
- the characterization of the MIP consists in demonstrating the formation of the imprints and in evaluating their number and their affinity for the targeted molecule. These results can be complemented by a study of the morphology of the material (size and shape of the particles, porosity and specific surface). These methods are known to a person skilled in the art (see, for example, point 1.7, p. 49, of the June 2010 doctoral thesis of R. Walsh, Development and Characterization of MIP http://repository.wit.ie/1619/1/Development and characterisation of molecularly imprinted suspension polymers.pdf)
- the cosmetic composition according to the invention comprises the molecularly imprinted polymer as described above and a physiologically acceptable medium.
- physiologically acceptable medium is understood to mean a medium compatible with cutaneous tissues, such as the skin and the scalp.
- the molecularly imprinted polymer according to the invention can be present in the cosmetic composition in a content ranging from 0.1% to 20% by weight, preferably ranging from 0.1% to 10% by weight and preferentially ranging from 0.1% to 5% by weight, with respect to the total weight of the composition.
- the physiologically acceptable medium of the composition can be more particularly composed of water and optionally of a physiologically acceptable organic solvent chosen, for example, from lower alcohols comprising from 2 to 8 carbon atoms and in particular from 2 to 6 carbon atoms, such as ethanol, isopropanol, propanol or butanol, polyethylene glycols having from 6 to 80 ethylene oxide units, and polyols, such as propylene glycol, isoprene glycol, butylene glycol, glycerol and sorbitol.
- a physiologically acceptable organic solvent chosen, for example, from lower alcohols comprising from 2 to 8 carbon atoms and in particular from 2 to 6 carbon atoms, such as ethanol, isopropanol, propanol or butanol, polyethylene glycols having from 6 to 80 ethylene oxide units, and polyols, such as propylene glycol, isoprene glycol, butylene glycol, glycerol and sorbitol.
- compositions according to the invention can be provided in all the formulation forms conventionally used for a topical application and in particular in the form of aqueous or aqueous/alcoholic solutions, of oil-in-water (O/W), water-in-oil (W/O) or multiple (triple: W/O/W or O/W/O) emulsions, of aqueous gels or of dispersions of a fatty phase in an aqueous phase using spherules, it being possible for these spherules to be polymeric nanoparticles, such as nanospheres and nanocapsules, or lipid vesicles of ionic and/or nonionic type (liposomes, niosomes or oleosomes). These compositions are prepared according to the usual methods.
- compositions used according to the invention can be more or less fluid and can have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a mousse or a shampoo.
- composition used according to the invention comprise adjuvants commonly employed in the cosmetics field and chosen in particular from water, oils, waxes, pigments, fillers, dyes, surfactants, emulsifiers, cosmetic active agents, UV-screening agents, polymers, thickeners, film-forming polymers, preservatives, fragrances, bactericides, odor absorbers or antioxidants.
- adjuvants commonly employed in the cosmetics field and chosen in particular from water, oils, waxes, pigments, fillers, dyes, surfactants, emulsifiers, cosmetic active agents, UV-screening agents, polymers, thickeners, film-forming polymers, preservatives, fragrances, bactericides, odor absorbers or antioxidants.
- composition according to the invention can comprise an additional antidandruff active agent chosen in particular from ellagic acid and its ethers, salts of ellagic acid and its ethers, pyrithione salts, 1-hydroxy-2-pyridone derivatives and selenium (poly)sulfides, and also their mixtures.
- an additional antidandruff active agent chosen in particular from ellagic acid and its ethers, salts of ellagic acid and its ethers, pyrithione salts, 1-hydroxy-2-pyridone derivatives and selenium (poly)sulfides, and also their mixtures.
- Ellagic acid or 2,3,7,8-tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione, is a well-known molecule which is present in the plant kingdom. Reference may be made to the publication of the Merck Index, 20th edition (1996), No. 3588. Ellagic acid exhibits the following chemical formula: which comprises four fused rings.
- the ellagic acid ether(s) which can be used according to the invention are preferably chosen from the mono-, di-, tri- or polyethers obtained by etherification of one or more hydroxyl groups (one of the four OH groups of ellagic acid) of ellagic acid to give one or more OR groups, R being chosen from C 2 -C 20 alkyl groups, polyoxyalkylene groups and in particular polyoxyethylene and/or polyoxypropylene groups, and groups derived from one or more mono- or polysaccharides, such as, for example, the group of following formula:
- the R groups as defined above can be identical or different.
- these ethers of ellagic acid are chosen from 3,4-di-O-methyl ellagic acid, 3,3',4-tri-O-methyl ellagic acid and 3,3'-di-O-methyl ellagic acid.
- the salt(s) of ellagic acid and/or of its ethers which can be used according to the invention are preferably chosen from alkali metal or alkaline earth metal salts, such as the sodium, potassium, calcium and magnesium salt, the ammonium salt and the salts of amines, such as triethanolamine, monoethanolamine, arginine and lysine salts.
- the salt(s) of ellagic acid and/or of its ethers which can be used according to the invention are chosen from alkali metal or alkaline earth metal salts, in particular the sodium, potassium, calcium or magnesium salts.
- Pyrithione is the compound 1-hydroxy-2(1H)-pyridinethione or 2-pyridinethiol 1-oxide.
- the pyrithione salts capable of being used in the context of the invention are in particular the monovalent metal salts and the divalent metal salts, such as the sodium, calcium, magnesium, barium, strontium, zinc, cadmium, tin and zirconium salts.
- the divalent metal salts and in particular the zinc salt (zinc pyrithione) are particularly preferred.
- the 1-hydroxy-2-pyridone derivatives are preferably chosen from the compounds of formula (A1) or their salts: in which:
- those which are particularly preferred consist of 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone and 6-cyclohexyl-1-hydroxy-4-methyl-2(1 H)-pyridone.
- Mention may be made, among the salts which can be used, of the salts of lower (C 1 -C 4 ) alkanolamines, such as ethanolamine and diethanolamine, amine or alkylamine salts, and also the salts with inorganic cations, such as ammonium salts and the salts of alkali metals or alkaline earth metals.
- Selenium disulfide is provided in the form of a powder, the particles of which generally have a particle size of less than 200 ⁇ m and preferably of less than 25 ⁇ m.
- the antidandruff agent is chosen from ellagic acid, zinc pyrithione, piroctone olamine and selenium disulfide, and also their mixture.
- the additional antidandruff active agents can be present in the composition according to the invention in a proportion of from 0.001% to 30% by weight and preferably in a proportion of from 0.5% to 25% by weight, with respect to the total weight of the composition.
- Example 1 (invention) and Example 2 (outside the invention):
- Example 1 The reactants and solvents were mixed in a beaker and then stirred at 60°C overnight. The reaction mixture was filtered and the precipitate was dried in an oven at 100°C overnight. After polymerization and attainment of the polymer impregnated with oleic acid, the impregnated polymer was washed 3 times with a 0.1 M ammonium hydroxide solution at 60°C and twice with methanol. Subsequently, the imprinted polymer, thus emptied of oleic acid, was dried under vacuum overnight. An oleic acid-imprinted polymer (MIP ex. 1) was obtained in the form of opaque white spherical particles. The mean diameter of the particles obtained is 1081 nm (determined by diffraction light scattering (DLS)).
- DLS diffraction light scattering
- Example 2 The same synthesis was carried out in the absence of the template (oleic acid) in order to prepare a non-imprinted polymer (NIP). This acts as reference (non-selective polymer). An opaque white polymer was obtained in the form of spherical particles. The mean diameter of the particles obtained is 1261 nm.
- An oleic acid-imprinted polymer (MIP ex. 3) and an imprint-free polymer (NIP ex. 4) were obtained in the form of opaque white spherical particles.
- the mean diameters of the particles are 332 nm (example 3) and 296 nm (example 4).
- the polymers obtained in the examples described above were suspended in a 5/55/40 (mixture by volume) propylene glycol/ethanol/water solution. Increasing concentrations of polymers were introduced into 2 ml polypropylene tubes, and [ 3 H]-oleic acid (0.45 nM, 15 nanoCuries) was added. The final volume was adjusted to 1 ml. The tubes were incubated overnight at ambient temperature on a rotary shaker. They were subsequently centrifuged at 16 000 g for 15 min and a 500 ⁇ l aliquot of the supernatant was withdrawn and transferred into a scintillation vial containing 3 ml of liquid scintillant (reference 327123 from Fluka).
- the amount of free radioligand was assayed by a scintillation counter (Beckman LS-6000 IC). This amount was compared with that of the solution of the [ 3 H]-oleic acid before it is brought into contact with the polymers. The difference makes it possible to evaluate the amount of [ 3 H]-oleic acid adsorbed.
- Figure 1A shows the variation in the amount of oleic acid adsorbed as a function of the concentration of polymer (MIP of example 1; NIP of example 2).
- Figure 1 B shows the change in the amount of oleic acid adsorbed as a function of the concentration of polymer (MIP of example 3; NIP of example 4).
- Example 8 Recognition at the surface of the stratum corneum
- the treated samples of stratum corneum were left in a closed petri dish for 3 hours and then washed twice with a propylene glycol/ethanol/water 5/55/40 solution (two times 2 ml) and then twice with a 5% by weight aqueous sodium lauryl sulfate solution (two times 1.5 ml). Subsequently, the pieces of stratum corneum were completely digested by Soluene®-350 solutions (1 ml, purchased from Sigma-Aldrich). Digestion took place at 40°C for 1.5 hours. The solutions obtained were added to scintillation solutions (5 ml, reference 327123 from Sigma-Aldrich) and the radioactivity was measured in a scintillation counter. Digestion is necessary in order to prevent interactions between the stratum corneum and the radiolabelled oleic acid, which can reduce the radioactivity measured.
- results obtained are interpreted in the following way: The higher the number of disintegrations per minute detected by the scintillation counter, the greater the radioactivity of the solution. A measured number of disintegrations per minute close to that of the control is interpreted as corresponding to no inhibition of the diffusion of the oleic acid in the stratum corneum. In this case, the oleic acid is not trapped by the polymer.
- a measured number of disintegrations per minute which is lower than that of the control is interpreted as a reduction in the diffusion of the oleic acid in the stratum corneum: it reflects the trapping of the oleic acid at the surface of the stratum corneum by the MIP.
- sample No. 1 (the control) should have the highest radioactivity.
- the NIP (sample No. 3) should not trap/inhibit the diffusion of the oleic acid in the skin and should thus have a figure close to or identical to sample No. 1.
- the MIP (sample No. 2) should have the least radioactivity as it was designed to trap the oleic acid.
- An antidandruff shampoo is prepared which comprises the following ingredients: Sodium lauryl ether sulfate (2.2 OE) as an aqueous solution 17 g AM (Texapon AOS 225 UP from Cognis) Coco-betaine as an aqueous solution (Dehyton AB 30 from Cognis) 2.5 g AM Coconut acid monoisopropanolamide (Rewomid V 3203 from Goldschmidt) 2.0 g Molecularly imprinted polymer of example 1 1 g AM Preservatives 1.1 g Fragrance 0.5 Water q.s. for 100 g
- the shampoo applied to the hair and the scalp, makes it possible to alleviate the appearance of dandruff.
- An antidandruff lotion is prepared which comprises the following ingredients:
- the lotion applied to the hair and the scalp, makes it possible to alleviate the appearance of dandruff.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1262784A FR2999920B1 (fr) | 2012-12-26 | 2012-12-26 | Polymeres a empreinte moleculaire de type solgel et leur utilisation comme agent antipelliculaire |
US201361773185P | 2013-03-06 | 2013-03-06 | |
PCT/EP2013/077790 WO2014102209A1 (en) | 2012-12-26 | 2013-12-20 | Molecularly imprinted polymers of sol-gel type and their use as antidandruff agent |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2938656A1 EP2938656A1 (en) | 2015-11-04 |
EP2938656B1 true EP2938656B1 (en) | 2016-08-24 |
Family
ID=48521063
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP13821474.7A Active EP2938656B1 (en) | 2012-12-26 | 2013-12-20 | Molecularly imprinted polymers of sol-gel type and their use as antidandruff agent |
Country Status (6)
Country | Link |
---|---|
US (2) | US20150342869A1 (zh) |
EP (1) | EP2938656B1 (zh) |
CN (1) | CN104870525B (zh) |
ES (1) | ES2602286T3 (zh) |
FR (1) | FR2999920B1 (zh) |
WO (1) | WO2014102209A1 (zh) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3000074B1 (fr) | 2012-12-26 | 2015-01-16 | Oreal | Polymeres a empreinte moleculaire et leur utilisation comme agent antipelliculaire |
FR2999917B1 (fr) | 2012-12-26 | 2017-06-23 | Oreal | Polymere a empreinte moleculaire pour pieger selectivement les molecules odorantes |
FR2999918B1 (fr) | 2012-12-26 | 2015-06-19 | Oreal | Polymere de type sol-gel a empreinte moleculaire pour pieger selectivement les molecules odorantes |
DE102013203484A1 (de) * | 2013-03-01 | 2014-09-04 | Henkel Ag & Co. Kgaa | Farbschützende Waschmittel |
US10768157B2 (en) | 2015-10-20 | 2020-09-08 | The Florida International University Board Of Trustees | Materials and methods for the detection of trace amounts of substances in biological and environmental samples |
US9772338B2 (en) * | 2015-10-20 | 2017-09-26 | The Florida International University Board Of Trustees | Materials and methods for the detection of trace amounts of substances in biological and environmental samples |
CN110183663B (zh) * | 2019-05-14 | 2022-07-19 | 浙江工业大学 | 一种芍药苷分子印迹聚合物及其制备与应用 |
CN115368619B (zh) * | 2022-08-09 | 2023-09-26 | 上海理工大学 | 一种分子印迹荧光传感器及其制备与应用 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6057377A (en) * | 1998-10-30 | 2000-05-02 | Sandia Corporation | Molecular receptors in metal oxide sol-gel materials prepared via molecular imprinting |
US6649212B2 (en) * | 2001-07-30 | 2003-11-18 | Guardian Industries Corporation | Modified silicon-based UV absorbers useful in crosslinkable polysiloxane coatings via sol-gel polymerization |
CN1252037C (zh) * | 2003-03-21 | 2006-04-19 | 清华大学 | 利用分子印迹法对神经酰胺进行分离纯化的方法 |
DE102004046179A1 (de) * | 2004-09-23 | 2006-03-30 | Wacker Chemie Ag | Vernetzbare Massen auf der Basis von Organosiliciumverbindungen |
EP2066406A2 (de) * | 2006-09-19 | 2009-06-10 | Basf Se | Kosmetische zubereitungen auf basis molekular geprägter polymere |
KR101520107B1 (ko) * | 2006-12-17 | 2015-05-13 | 가부시키가이샤 브리지스톤 | 혼성 중합체 및 제조방법 |
US8679859B2 (en) * | 2007-03-12 | 2014-03-25 | State of Oregon by and through the State Board of Higher Education on behalf of Porland State University | Method for functionalizing materials and devices comprising such materials |
FR2930438B1 (fr) * | 2008-04-25 | 2012-09-21 | Oreal | Composition cosmetique comprenant au moins un compose organique du silicium, au moins un tensioactif cationique et au moins un acide organique, et un procede de traitement cosmetique mettant en oeuvre ladite composition |
FR2941621B1 (fr) * | 2009-01-30 | 2011-04-01 | Oreal | Composition cosmetique comprenant un alkoxysilane particulier et une gomme microbienne et utilisations en coiffage |
CN101906186B (zh) * | 2010-08-11 | 2012-08-29 | 天津科技大学 | 脂肪酸类分子印迹聚合物的制备方法 |
FR2975593B1 (fr) * | 2011-05-27 | 2013-05-10 | Oreal | Composition comprenant un alcoxysilane et un amidon modifie et son utilisation en cosmetique |
FR2975594B1 (fr) * | 2011-05-27 | 2013-05-10 | Oreal | Composition comprenant un alcoxysilane, un ester gras et une silicone et son utilisation en cosmetique |
CN102585156B (zh) * | 2012-02-22 | 2013-09-11 | 天津科技大学 | 一种α-亚麻酸分子印迹聚合物材料的制备方法 |
-
2012
- 2012-12-26 FR FR1262784A patent/FR2999920B1/fr not_active Expired - Fee Related
-
2013
- 2013-12-20 CN CN201380068333.1A patent/CN104870525B/zh active Active
- 2013-12-20 US US14/655,395 patent/US20150342869A1/en not_active Abandoned
- 2013-12-20 ES ES13821474.7T patent/ES2602286T3/es active Active
- 2013-12-20 EP EP13821474.7A patent/EP2938656B1/en active Active
- 2013-12-20 WO PCT/EP2013/077790 patent/WO2014102209A1/en active Application Filing
-
2018
- 2018-12-04 US US16/208,709 patent/US20190125655A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
FR2999920B1 (fr) | 2015-07-17 |
ES2602286T3 (es) | 2017-02-20 |
CN104870525A (zh) | 2015-08-26 |
US20190125655A1 (en) | 2019-05-02 |
FR2999920A1 (fr) | 2014-06-27 |
WO2014102209A1 (en) | 2014-07-03 |
US20150342869A1 (en) | 2015-12-03 |
CN104870525B (zh) | 2017-09-19 |
EP2938656A1 (en) | 2015-11-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2938656B1 (en) | Molecularly imprinted polymers of sol-gel type and their use as antidandruff agent | |
EP3261611B1 (de) | Zusammensetzung enthaltend rhamnolipid und siloxan | |
EP2449079B1 (en) | Cationic synthetic polymers with improved solubility and performance in surfactant-based systems and use in personal care and household applications | |
DE3853373T2 (de) | Kombinationen von Glycosaminoglycan mit kationischen Polymeren. | |
US11246823B2 (en) | Molecularly imprinted polymer of sol-gel type for selectively trapping odorous molecules | |
EP2073785B1 (en) | Quaternized cellulose ethers for personal care products | |
CN101690697B (zh) | 去屑洗发组合物 | |
EP3709960B1 (en) | Hair care composition | |
CN102065833A (zh) | 洗发香波制剂 | |
US4411891A (en) | Cationized dextran and salts thereof and manufacturing process and utilization thereof | |
CN102065834A (zh) | 洗发香波制剂 | |
EP2938641B1 (en) | Molecularly imprinted polymers and their use as antidandruff agents | |
WO2009100464A4 (en) | Compositions containing cationically surface-modified microparticulate carrier for benefit agents | |
EP2794012B1 (fr) | Utilisation de polysaccharides sulfatés comme agent antipelliculaire | |
JP6246474B2 (ja) | 多糖体,皮膚バリア機能改善剤及び皮膚保湿剤 | |
DE69800050T2 (de) | Poly(N-acylalkylenimin) modifizierte Organopolysiloxane | |
JP2018536662A (ja) | 毛髪ケア組成物 | |
Brandão et al. | Acetylated cashew-gum-based silver nanoparticles for the development of latent fingerprints on porous surfaces | |
JPS643193B2 (zh) | ||
CN113226477B (zh) | 包含吡啶硫酮的毛发护理组合物 | |
JP2018024707A (ja) | 皮膚バリア機能改善剤及び皮膚保湿剤 | |
BR112020009304B1 (pt) | Composição para cuidados do cabelo, método de deposição de agentes anticaspa e uso da composição para cuidados do cabelo | |
CN106860052A (zh) | 化妆品用颗粒乳化剂的制备方法 | |
TW201918245A (zh) | 防微塵組成物 | |
JP2018145281A (ja) | ブロック共重合体、及びポリマーミセル、並びに薬粧品組成物、及び経皮吸収用製剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20150727 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAX | Request for extension of the european patent (deleted) | ||
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
INTG | Intention to grant announced |
Effective date: 20160512 |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: REF Ref document number: 823051 Country of ref document: AT Kind code of ref document: T Effective date: 20160915 |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602013010788 Country of ref document: DE |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 4 |
|
REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG4D |
|
REG | Reference to a national code |
Ref country code: NL Ref legal event code: MP Effective date: 20160824 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 823051 Country of ref document: AT Kind code of ref document: T Effective date: 20160824 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: RS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: NO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161124 Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: HR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2602286 Country of ref document: ES Kind code of ref document: T3 Effective date: 20170220 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161125 Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161226 Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R097 Ref document number: 602013010788 Country of ref document: DE |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: PL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: SM Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20161124 Ref country code: BE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
26N | No opposition filed |
Effective date: 20170526 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: MM4A |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20161231 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20161231 Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20161220 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 5 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20161220 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: HU Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO Effective date: 20131220 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: MK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: CY Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20161220 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 Ref country code: TR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20160824 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20231026 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: IT Payment date: 20231110 Year of fee payment: 11 Ref country code: FR Payment date: 20231108 Year of fee payment: 11 Ref country code: DE Payment date: 20231024 Year of fee payment: 11 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 20240116 Year of fee payment: 11 |